4-(Chloromethyl)pyridine → 3-(Benzhydrylidene-amino)-3-pyridin-4-ylmethyl-dihydro-furan-2-one

HRID 566465Notes

Reaction equation

C[Si]([N-][Si](C)(C)C)(C)C.[K+].[C:11](=[N:24][CH:25]1[CH2:29][CH2:28][O:27][C:26]1=[O:30])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[N:31]1[CH:36]=[CH:35][C:34]([CH2:37]Cl)=[CH:33][CH:32]=1>C1COCC1>[C:11](=[N:24][C:25]1([CH2:37][C:34]2[CH:35]=[CH:36][N:31]=[CH:32][CH:33]=2)[CH2:29][CH2:28][O:27][C:26]1=[O:30])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 40 °C

Procedure

Potassium bis-(trimethylsilyl)amide (2.67, 13.4 mMol) was dissolved in anhydrous THF (50 mL) under an atmosphere of dry N2. The mixture was cooled to 40° C. to which was added a solution of 3-(benzhydrylidene-amino)-dihydro-furan-2-one (3.38 g, 12.7 mMol) in THF (30 mL). The mixture was warmed to ambient temperature and stirred at this temperature for 30 minutes. The solution was then cooled to 40° C. and a solution of 4-picolyl chloride (1.70 g, 13.4 mMol) in THF (20 mL) was added. The reaction mixture was warmed to ambient temperature and stirred for 18 hours. The mixture was partitioned between ethyl acetate-(EtOAc) and water.

Workup

temperatureThe mixture was warmed to ambient temperature
temperatureThe solution was then cooled to 40° C.
temperatureThe reaction mixture was warmed to ambient temperature
stirringstirred for 18 hours
customThe mixture was partitioned between ethyl acetate-(EtOAc) and water

Sources & evidence

ORD record: ord-485d855ff9f3463d8bcb164ec2483dcb
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06174903B1

Reaction notes

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